Somebody has to plan this.
Might as well be good.

The best man doesn't front the trip, and the groom doesn't pay his own way — two separate myths that cause two separate arguments. Most groups split lodging and shared meals evenly across everyone attending, including the groom, and let people cover their own flights, bar tabs and side activities.

Collect money before you book anything, not after. A shared spreadsheet or a simple per-person number quoted up front avoids the awkward chase for payment in week two.

If someone wants a bigger room or skips an activity, handle it as a line-item adjustment, not a separate negotiation with the whole group.

Between the invite and the flight, at least one person usually cancels — a new job, a new baby, money. Build the group size with a little room in it rather than booking to the exact headcount you have today.

Lodging and shared bookings are easiest to adjust when they're held rather than fully paid weeks out. Ask about cancellation terms before you commit the group's money, not after.

Decide, before it happens, whether the remaining group absorbs the shared costs or the person who dropped covers their share. That's a much easier conversation to have in advance than in the moment.

Vegas is easy to book and hard to get wrong logistically, which is exactly why it's the default answer. It's also not the only good one, and for a group that wants to remember the weekend for something other than the hangover, it's often not the best.

A mountain town gives everyone a full day of something physical before the group reconvenes for dinner. A food city gives you a reason to book somewhere with real restaurants instead of another buffet. Links golf gives the golfers in the group an actual reason to fly somewhere.

Pick the destination for the group you have, not the group you assume you have. A quiet crew of six wants something different than a sixteen-person blowout — tell us which one you're planning for.